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Showing Compound p-Mentha-1,8-dien-7-ol (FDB014923)

Record Information
Version1.0
Creation date2010-04-08 22:11:33 UTC
Update date2019-11-26 03:10:57 UTC
Primary IDFDB014923
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namep-Mentha-1,8-dien-7-ol
DescriptionPerillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID: 9855569) [HMDB]. p-Mentha-1,8-dien-7-ol is found in many foods, some of which are caraway, ginger, german camomile, and sweet bay.
CAS Number536-59-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-Hydroxymethyl-4-isopropenyl-1-cyclohexeneChEBI
1-PerillalcoholChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-methanolChEBI
4-Isopropenyl-1-cyclohexene carbinolChEBI
4-Isopropenylcyclohex-1-en-1-ylmethanolChEBI
Dihydrocuminyl alcoholnChEBI
IsocarveolChEBI
p-Mentha-1,8-dien-7-olChEBI
Perilla alcoholChEBI
PerillolChEBI
(-)-Perillyl alcoholHMDB
(S)-(-)-Perillyl alcoholHMDB
1,8-p-Menthadien-7-olHMDB
4-Isopropenyl-cyclohex-1-ene-1-methanolHMDB
Dihydrocuminic alcoholHMDB
Dihydrocuminyl alcoholHMDB
Hydrocumin alcoholHMDB
Iso-carveolHMDB
Para-mentha-1,8-dien-7-olHMDB
Perill alcoholHMDB
Perillic alcoholHMDB
Cyclohex-1-ene-1-methanol, 4(1-methylethenyl)HMDB
Perilla alcohol, (S)-isomerHMDB
Perilla alcohol, (R)-isomerHMDB
(-)-p-Mentha-1,8-dien-7-olHMDB
(S)-Perillyl alcoholHMDB
1-Hydroxymethyl-4-isopropenylcyclohexenedb_source
1,8-P-Menthadien-7-olHMDB
4-(1-Methylethenyl)-1-cyclohexene-1-methanol, 9CIdb_source
NSC 641066db_source
Perillyl alcoholdb_source
Predicted Properties
PropertyValueSource
Water Solubility1.9 g/LALOGPS
logP2.5ALOGPS
logP1.94ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)16.86ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.26 m³·mol⁻¹ChemAxon
Polarizability18.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
InChI IdentifierInChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
InChI KeyNDTYTMIUWGWIMO-UHFFFAOYSA-N
Isomeric SMILESCC(=C)C1CCC(CO)=CC1
Average Molecular Weight152.237
Monoisotopic Molecular Weight152.120115135
Classification
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSp-Mentha-1,8-dien-7-ol, 1 TMS, GC-MS Spectrumsplash10-0006-9600000000-852faf99c20eb91e9836Spectrum
GC-MSp-Mentha-1,8-dien-7-ol, non-derivatized, GC-MS Spectrumsplash10-00mo-9200000000-6d3cda5b991dc6f0a098Spectrum
GC-MSp-Mentha-1,8-dien-7-ol, non-derivatized, GC-MS Spectrumsplash10-014l-9300000000-f32f7e87d33288c8045dSpectrum
GC-MSp-Mentha-1,8-dien-7-ol, non-derivatized, GC-MS Spectrumsplash10-0006-9600000000-852faf99c20eb91e9836Spectrum
Predicted GC-MSp-Mentha-1,8-dien-7-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007x-9400000000-0642824f11b9c7fd315dSpectrum
Predicted GC-MSp-Mentha-1,8-dien-7-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05gu-9510000000-9f19c403be332e74c8adSpectrum
Predicted GC-MSp-Mentha-1,8-dien-7-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00du-3900000000-a6c07543feea874fe65d2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004u-9000000000-352e042e70150a70fc172012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bvj-9000000000-9a2da0a6d60335f43f462012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-00mo-9200000000-81544f3016fa24bad81f2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-1900000000-2f012741782fc72aa3df2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-849092ef4eeddd4406872016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-9200000000-fd4b15fd9437d4b704092016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-20d0d9f448f90e31136f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-0900000000-a390120b9758e2ca2f5d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-39d18f7a3231672157f52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-8fa95dbd5fa627e933fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9200000000-7da801ed46abad2dd6282021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f84-9800000000-bd8e7097a31172f8ad0e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-373d4892dedc5ff6266f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-a6d86d2ceee0f1021fd32021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID10362
ChEMBL IDCHEMBL444711
KEGG Compound IDC02452
Pubchem Compound ID10819
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03634
CRC / DFC (Dictionary of Food Compounds) IDJXK16-E:JXK16-E
EAFUS ID2132
Dr. Duke IDP-MENTHA-1-8-DIEN-7-OL|MENTHADIEN-1,8(9)-OL-(7)|PERILLYL-ALCOHOL
BIGG ID39849
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1031131
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti proliferantDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
apoptoticDUKE
candidicideDUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
linalool
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpineol
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).